# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_MX16_21A
_database_code_depnum_ccdc_archive 'CCDC 2121689'
loop_
_audit_author_name
_audit_author_address
'Craig Forsyth'
;Monash University
Australia
;
_audit_update_record             
;
2021-11-11 deposited with the CCDC.	2022-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H14 N O, B F4'
_chemical_formula_sum            'C5 H14 B F4 N O'
_chemical_formula_weight         190.98

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.8883(3)
_cell_length_b                   11.8590(3)
_cell_length_c                   11.5357(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.952(3)
_cell_angle_gamma                90
_cell_volume                     1807.45(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    8574
_cell_measurement_theta_min      4.9830
_cell_measurement_theta_max      76.6540

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.314
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.70817
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            18973
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.011
_diffrn_reflns_theta_max         77.347
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3755
_reflns_number_gt                3162
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The two unique BF4 anions were both modelled as rotationally disordered with the 
fluorine atoms each in two positions with refined occupancies approximately 0.5:0.5.
One of the Me3NCH2OCH3 cations was also modelled as disordered with one Me group and
the CH2OCH3 group in two positions with refined occupancies approximately 0.75:0.25. 
The diosredered N-CH3 moiety was refined with restrained N-C distances (SADI) and 
anisotropic displacement parameters (SIMU).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0855P)²+0.7283P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3755
_refine_ls_number_parameters     338
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1661
_refine_ls_wR_factor_gt          0.1593
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.142
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.61133(19) 0.2047(3) 0.3118(3) 0.0470(9) Uani 0.511(7) 1 d . . P A 1
F1A F 0.5769(6) 0.2529(5) 0.3327(3) 0.094(2) Uani 0.489(7) 1 d . . P A 2
F2 F 0.4555(5) 0.1289(7) 0.2923(9) 0.094(3) Uani 0.511(7) 1 d . . P A 1
F2A F 0.4553(4) 0.1427(7) 0.3175(8) 0.073(2) Uani 0.489(7) 1 d . . P A 2
F3 F 0.4791(3) 0.3162(3) 0.2409(5) 0.0677(14) Uani 0.511(7) 1 d . . P A 1
F3A F 0.4400(3) 0.2684(4) 0.1710(4) 0.0753(14) Uani 0.489(7) 1 d . . P A 2
F4 F 0.5027(3) 0.1761(5) 0.1288(3) 0.0747(14) Uani 0.511(7) 1 d . . P A 1
F4A F 0.5408(4) 0.1262(4) 0.1824(6) 0.0820(14) Uani 0.489(7) 1 d . . P A 2
F5 F 1.1496(8) 0.2335(8) 0.6850(10) 0.065(2) Uani 0.488(17) 1 d . . P B 1
F5A F 1.1622(7) 0.2435(8) 0.6727(10) 0.0555(16) Uani 0.512(17) 1 d . . P B 2
F6 F 1.0542(4) 0.0772(6) 0.6011(5) 0.0492(13) Uani 0.488(17) 1 d . . P B 1
F6A F 1.0364(3) 0.1200(8) 0.6337(6) 0.0522(17) Uani 0.512(17) 1 d . . P B 2
F7 F 0.9896(3) 0.2523(6) 0.5521(5) 0.0401(12) Uani 0.488(17) 1 d . . P B 1
F7A F 1.0182(8) 0.2828(5) 0.5305(5) 0.0575(18) Uani 0.512(17) 1 d . . P B 2
F8 F 1.1119(6) 0.1835(8) 0.4772(7) 0.0477(13) Uani 0.488(17) 1 d . . P B 1
F8A F 1.1233(7) 0.1538(10) 0.5039(10) 0.068(2) Uani 0.512(17) 1 d . . P B 2
O1 O 0.81972(9) 0.03303(11) 0.78709(10) 0.0378(3) Uani 1 1 d . . . . .
O2 O 0.83783(17) 0.1079(2) 0.16534(18) 0.0415(6) Uani 0.747(5) 1 d . . P C 1
O2A O 0.7961(5) 0.1443(5) 0.1926(6) 0.0459(18) Uani 0.253(5) 1 d . . P C 2
N1 N 0.71517(10) 0.02924(12) 0.58024(12) 0.0317(3) Uani 1 1 d . . . . .
N2 N 0.71704(10) -0.02399(14) 0.07882(13) 0.0380(4) Uani 1 1 d D . . . .
C1 C 0.78829(14) 0.09636(17) 0.53582(16) 0.0409(4) Uani 1 1 d . . . . .
H1A H 0.751412 0.136532 0.461081 0.061 Uiso 1 1 calc R U . . .
H1B H 0.837942 0.045479 0.518921 0.061 Uiso 1 1 calc R U . . .
H1C H 0.823312 0.150931 0.598420 0.061 Uiso 1 1 calc R U . . .
C2 C 0.65910(13) -0.05205(17) 0.48363(16) 0.0397(4) Uani 1 1 d . . . . .
H2A H 0.613152 -0.097487 0.514172 0.059 Uiso 1 1 calc R U . . .
H2B H 0.707524 -0.101642 0.462332 0.059 Uiso 1 1 calc R U . . .
H2C H 0.619946 -0.010203 0.411178 0.059 Uiso 1 1 calc R U . . .
C3 C 0.64152(13) 0.10658(16) 0.61105(17) 0.0388(4) Uani 1 1 d . . . . .
H3A H 0.603610 0.148585 0.538095 0.058 Uiso 1 1 calc R U . . .
H3B H 0.678281 0.159570 0.674450 0.058 Uiso 1 1 calc R U . . .
H3C H 0.594409 0.062242 0.640773 0.058 Uiso 1 1 calc R U . . .
C4 C 0.77138(13) -0.03893(15) 0.69241(15) 0.0349(4) Uani 1 1 d . . . . .
H4A H 0.722992 -0.087301 0.717126 0.042 Uiso 1 1 calc R U . . .
H4B H 0.821851 -0.088350 0.673155 0.042 Uiso 1 1 calc R U . . .
C5 C 0.92868(13) 0.02637(19) 0.82519(17) 0.0442(5) Uani 1 1 d . . . . .
H5A H 0.950066 -0.049733 0.855409 0.066 Uiso 1 1 calc R U . . .
H5B H 0.957043 0.081286 0.890252 0.066 Uiso 1 1 calc R U . . .
H5C H 0.952989 0.043028 0.755792 0.066 Uiso 1 1 calc R U . . .
C6 C 0.66133(13) 0.05362(17) -0.02224(16) 0.0408(4) Uani 1 1 d . . . . .
H6A H 0.619249 0.009125 -0.090794 0.061 Uiso 1 1 calc R U . . .
H6B H 0.710119 0.098005 -0.048999 0.061 Uiso 1 1 calc R U . . .
H6C H 0.618211 0.104447 0.007012 0.061 Uiso 1 1 calc R U . . .
C7 C 0.7821(2) -0.10255(19) 0.0380(2) 0.0573(6) Uani 1 1 d . . . . .
H7A H 0.814745 -0.154809 0.104285 0.086 Uiso 1 1 calc R U . . .
H7B H 0.833935 -0.059912 0.015254 0.086 Uiso 1 1 calc R U . . .
H7C H 0.740798 -0.145216 -0.032588 0.086 Uiso 1 1 calc R U . . .
C8 C 0.6407(2) -0.1025(3) 0.1141(3) 0.0447(7) Uani 0.747(5) 1 d D U P C 1
H8A H 0.604811 -0.148881 0.043816 0.067 Uiso 0.747(5) 1 calc R U P C 1
H8B H 0.591901 -0.056545 0.139109 0.067 Uiso 0.747(5) 1 calc R U P C 1
H8C H 0.677485 -0.151452 0.181737 0.067 Uiso 0.747(5) 1 calc R U P C 1
C8A C 0.6622(7) -0.0476(9) 0.1555(8) 0.0443(17) Uani 0.253(5) 1 d D U P C 2
H8A1 H 0.599488 -0.086186 0.110302 0.067 Uiso 0.253(5) 1 calc R U P C 2
H8A2 H 0.645835 0.022736 0.189868 0.067 Uiso 0.253(5) 1 calc R U P C 2
H8A3 H 0.701932 -0.096395 0.221589 0.067 Uiso 0.253(5) 1 calc R U P C 2
C9 C 0.76808(16) 0.0376(2) 0.1943(2) 0.0374(7) Uani 0.747(5) 1 d . . P C 1
H9A H 0.718541 0.082269 0.221057 0.045 Uiso 0.747(5) 1 calc R U P C 1
H9B H 0.802719 -0.015698 0.259962 0.045 Uiso 0.747(5) 1 calc R U P C 1
C9A C 0.8225(6) 0.0510(10) 0.1366(8) 0.039(2) Uani 0.253(5) 1 d . . P C 2
H9A1 H 0.874307 0.005539 0.196601 0.047 Uiso 0.253(5) 1 calc R U P C 2
H9A2 H 0.850286 0.074933 0.071127 0.047 Uiso 0.253(5) 1 calc R U P C 2
C10 C 0.9017(5) 0.1625(5) 0.2722(6) 0.0460(12) Uani 0.747(5) 1 d . . P C 1
H10A H 0.860277 0.209084 0.308542 0.069 Uiso 0.747(5) 1 calc R U P C 1
H10B H 0.950805 0.210414 0.249974 0.069 Uiso 0.747(5) 1 calc R U P C 1
H10C H 0.937745 0.105520 0.331116 0.069 Uiso 0.747(5) 1 calc R U P C 1
C10A C 0.8799(12) 0.1855(13) 0.2873(14) 0.036(3) Uani 0.253(5) 1 d . . P C 2
H10D H 0.908546 0.124424 0.344925 0.055 Uiso 0.253(5) 1 calc R U P C 2
H10E H 0.857820 0.246909 0.329973 0.055 Uiso 0.253(5) 1 calc R U P C 2
H10F H 0.931500 0.213575 0.252671 0.055 Uiso 0.253(5) 1 calc R U P C 2
B1 B 0.50559(14) 0.20174(17) 0.24782(17) 0.0330(4) Uani 1 1 d . . . . .
B2 B 1.08030(14) 0.19343(16) 0.58219(17) 0.0317(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.426(3) . ?
F1A B1 1.307(4) . ?
F2 B1 1.309(7) . ?
F2A B1 1.404(7) . ?
F3 B1 1.403(4) . ?
F3A B1 1.320(4) . ?
F4 B1 1.394(3) . ?
F4A B1 1.356(4) . ?
F5 B2 1.362(10) . ?
F5A B2 1.416(10) . ?
F6 B2 1.459(5) . ?
F6A B2 1.306(3) . ?
F7 B2 1.387(4) . ?
F7A B2 1.381(4) . ?
F8 B2 1.414(9) . ?
F8A B2 1.314(9) . ?
O1 C4 1.386(2) . ?
O1 C5 1.442(2) . ?
O2 C9 1.395(3) . ?
O2 C10 1.432(7) . ?
O2A C9A 1.386(12) . ?
O2A C10A 1.416(18) . ?
N1 C3 1.496(2) . ?
N1 C2 1.497(2) . ?
N1 C1 1.499(2) . ?
N1 C4 1.521(2) . ?
N2 C8A 1.362(6) . ?
N2 C7 1.472(2) . ?
N2 C9 1.493(3) . ?
N2 C6 1.500(2) . ?
N2 C8 1.556(3) . ?
N2 C9A 1.667(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C5 114.49(13) . . ?
C9 O2 C10 110.9(3) . . ?
C9A O2A C10A 111.2(8) . . ?
C3 N1 C2 109.55(13) . . ?
C3 N1 C1 109.91(14) . . ?
C2 N1 C1 109.82(13) . . ?
C3 N1 C4 109.44(12) . . ?
C2 N1 C4 107.68(13) . . ?
C1 N1 C4 110.41(12) . . ?
C8A N2 C7 126.7(4) . . ?
C7 N2 C9 115.18(17) . . ?
C8A N2 C6 111.9(4) . . ?
C7 N2 C6 111.12(15) . . ?
C9 N2 C6 112.51(16) . . ?
C7 N2 C8 103.85(19) . . ?
C9 N2 C8 103.50(17) . . ?
C6 N2 C8 109.93(15) . . ?
C8A N2 C9A 116.6(5) . . ?
C7 N2 C9A 85.2(4) . . ?
C6 N2 C9A 99.4(3) . . ?
O1 C4 N1 109.88(14) . . ?
O2 C9 N2 104.64(18) . . ?
O2A C9A N2 106.6(5) . . ?
F1A B1 F3A 115.6(3) . . ?
F1A B1 F4A 113.8(4) . . ?
F3A B1 F4A 108.4(3) . . ?
F2 B1 F4 112.6(5) . . ?
F2 B1 F3 119.9(4) . . ?
F4 B1 F3 103.2(3) . . ?
F1A B1 F2A 101.4(5) . . ?
F3A B1 F2A 108.7(3) . . ?
F4A B1 F2A 108.5(4) . . ?
F2 B1 F1 113.6(4) . . ?
F4 B1 F1 103.2(2) . . ?
F3 B1 F1 102.5(2) . . ?
F6A B2 F8A 116.7(4) . . ?
F6A B2 F7A 113.0(3) . . ?
F8A B2 F7A 109.5(4) . . ?
F5 B2 F7 112.7(4) . . ?
F5 B2 F8 116.9(7) . . ?
F7 B2 F8 109.0(4) . . ?
F6A B2 F5A 109.0(4) . . ?
F8A B2 F5A 103.0(6) . . ?
F7A B2 F5A 104.4(5) . . ?
F5 B2 F6 109.9(4) . . ?
F7 B2 F6 105.3(2) . . ?
F8 B2 F6 101.9(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C4 N1 -115.06(15) . . . . ?
C3 N1 C4 O1 -57.43(17) . . . . ?
C2 N1 C4 O1 -176.44(13) . . . . ?
C1 N1 C4 O1 63.67(17) . . . . ?
C10 O2 C9 N2 -172.8(3) . . . . ?
C7 N2 C9 O2 66.8(2) . . . . ?
C6 N2 C9 O2 -62.0(2) . . . . ?
C8 N2 C9 O2 179.4(2) . . . . ?
C10A O2A C9A N2 153.8(7) . . . . ?
C8A N2 C9A O2A -50.2(8) . . . . ?
C7 N2 C9A O2A -179.2(6) . . . . ?
C6 N2 C9A O2A 70.1(6) . . . . ?

_refine_diff_density_max         0.570
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.050

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_MX14_21_a
_database_code_depnum_ccdc_archive 'CCDC 2121690'
loop_
_audit_author_name
_audit_author_address
'Craig Forsyth'
;Monash University
Australia
;
_audit_update_record             
;
2021-11-11 deposited with the CCDC.	2022-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'F6 P, C5 H14 N O'
_chemical_formula_sum            'C5 H14 F6 N O P'
_chemical_formula_weight         249.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4903(3)
_cell_length_b                   10.4513(3)
_cell_length_c                   12.5101(5)
_cell_angle_alpha                66.584(3)
_cell_angle_beta                 83.725(3)
_cell_angle_gamma                89.254(3)
_cell_volume                     1011.99(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    7561
_cell_measurement_theta_min      3.8640
_cell_measurement_theta_max      77.0030

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.313
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.019
_exptl_absorpt_coefficient_mu    3.084
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.55201
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            21091
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.876
_diffrn_reflns_theta_max         77.230
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4207
_reflns_number_gt                3615
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0566P)²+0.3017P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4207
_refine_ls_number_parameters     261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.22404(5) 0.07721(4) 0.15261(4) 0.02447(12) Uani 1 1 d . . . . .
P2 P 0.28733(5) 0.60325(4) 0.70436(4) 0.02417(12) Uani 1 1 d . . . . .
F1 F 0.20978(14) -0.05526(11) 0.27498(10) 0.0389(3) Uani 1 1 d . . . . .
F2 F 0.06702(13) 0.13625(12) 0.19671(10) 0.0400(3) Uani 1 1 d . . . . .
F3 F 0.11916(14) -0.00364(12) 0.09895(11) 0.0421(3) Uani 1 1 d . . . . .
F4 F 0.38067(13) 0.01713(12) 0.10824(11) 0.0413(3) Uani 1 1 d . . . . .
F5 F 0.32990(14) 0.15769(11) 0.20543(10) 0.0399(3) Uani 1 1 d . . . . .
F6 F 0.23756(13) 0.21033(11) 0.03076(9) 0.0353(2) Uani 1 1 d . . . . .
F7 F 0.29058(14) 0.45033(11) 0.80661(10) 0.0374(3) Uani 1 1 d . . . . .
F8 F 0.14672(14) 0.64093(12) 0.78181(10) 0.0406(3) Uani 1 1 d . . . . .
F9 F 0.15953(13) 0.54628(12) 0.64749(10) 0.0362(2) Uani 1 1 d . . . . .
F10 F 0.42680(13) 0.56305(11) 0.62791(10) 0.0364(3) Uani 1 1 d . . . . .
F11 F 0.41402(15) 0.65730(13) 0.76355(11) 0.0440(3) Uani 1 1 d . . . . .
F12 F 0.28350(15) 0.75471(11) 0.60243(10) 0.0401(3) Uani 1 1 d . . . . .
O1 O 0.21756(16) 0.65196(12) 0.27013(11) 0.0322(3) Uani 1 1 d . . . . .
O2 O 0.19370(17) 0.24172(13) 0.51494(12) 0.0378(3) Uani 1 1 d . . . . .
N1 N 0.23853(16) 0.60100(13) 0.10470(12) 0.0242(3) Uani 1 1 d . . . . .
N2 N 0.29951(16) 0.13305(14) 0.69852(13) 0.0262(3) Uani 1 1 d . . . . .
C1 C 0.2482(2) 0.47975(18) 0.06927(16) 0.0328(4) Uani 1 1 d . . . . .
H1A H 0.341255 0.425805 0.098037 0.049 Uiso 1 1 calc R U . . .
H1B H 0.257581 0.514063 -0.016411 0.049 Uiso 1 1 calc R U . . .
H1C H 0.152222 0.420084 0.103001 0.049 Uiso 1 1 calc R U . . .
C2 C 0.0955(2) 0.68260(18) 0.06194(16) 0.0315(4) Uani 1 1 d . . . . .
H2A H -0.000147 0.622834 0.097325 0.047 Uiso 1 1 calc R U . . .
H2B H 0.102848 0.715703 -0.023597 0.047 Uiso 1 1 calc R U . . .
H2C H 0.090141 0.762699 0.084104 0.047 Uiso 1 1 calc R U . . .
C3 C 0.3849(2) 0.69308(19) 0.05345(16) 0.0320(4) Uani 1 1 d . . . . .
H3A H 0.375373 0.774578 0.073633 0.048 Uiso 1 1 calc R U . . .
H3B H 0.397306 0.723941 -0.032013 0.048 Uiso 1 1 calc R U . . .
H3C H 0.477636 0.640922 0.085230 0.048 Uiso 1 1 calc R U . . .
C4 C 0.2255(2) 0.54035(16) 0.23588(14) 0.0268(3) Uani 1 1 d . . . . .
H4A H 0.129039 0.479231 0.269295 0.032 Uiso 1 1 calc R U . . .
H4B H 0.319055 0.484388 0.263580 0.032 Uiso 1 1 calc R U . . .
C5 C 0.2026(2) 0.60405(18) 0.39444(15) 0.0298(4) Uani 1 1 d . . . . .
H5A H 0.103582 0.548666 0.427943 0.045 Uiso 1 1 calc R U . . .
H5B H 0.201420 0.684276 0.416375 0.045 Uiso 1 1 calc R U . . .
H5C H 0.292528 0.546213 0.424628 0.045 Uiso 1 1 calc R U . . .
C6 C 0.4469(2) 0.22330(19) 0.65036(18) 0.0353(4) Uani 1 1 d . . . . .
H6A H 0.534938 0.175677 0.693274 0.053 Uiso 1 1 calc R U . . .
H6B H 0.430385 0.311788 0.659091 0.053 Uiso 1 1 calc R U . . .
H6C H 0.472026 0.241633 0.567124 0.053 Uiso 1 1 calc R U . . .
C7 C 0.2597(2) 0.1077(2) 0.82479(17) 0.0374(4) Uani 1 1 d . . . . .
H7A H 0.161844 0.050108 0.856120 0.056 Uiso 1 1 calc R U . . .
H7B H 0.244780 0.197085 0.832130 0.056 Uiso 1 1 calc R U . . .
H7C H 0.346410 0.059173 0.868932 0.056 Uiso 1 1 calc R U . . .
C8 C 0.3249(2) -0.00246(18) 0.68684(19) 0.0368(4) Uani 1 1 d . . . . .
H8A H 0.412285 -0.049862 0.730756 0.055 Uiso 1 1 calc R U . . .
H8B H 0.351254 0.014730 0.603924 0.055 Uiso 1 1 calc R U . . .
H8C H 0.227997 -0.061308 0.718159 0.055 Uiso 1 1 calc R U . . .
C9 C 0.1623(2) 0.20880(18) 0.63320(16) 0.0308(4) Uani 1 1 d . . . . .
H9A H 0.064747 0.148763 0.664375 0.037 Uiso 1 1 calc R U . . .
H9B H 0.143654 0.295337 0.646434 0.037 Uiso 1 1 calc R U . . .
C10 C 0.1073(3) 0.1603(2) 0.4705(2) 0.0498(5) Uani 1 1 d . . . . .
H10A H 0.126579 0.061207 0.513217 0.075 Uiso 1 1 calc R U . . .
H10B H 0.142530 0.187773 0.386926 0.075 Uiso 1 1 calc R U . . .
H10C H -0.006237 0.176364 0.480959 0.075 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 F5 1.5947(11) . ?
P1 F2 1.5971(11) . ?
P1 F6 1.5978(11) . ?
P1 F1 1.5982(11) . ?
P1 F3 1.5996(11) . ?
P1 F4 1.6015(11) . ?
P2 F12 1.5926(11) . ?
P2 F11 1.5959(12) . ?
P2 F10 1.5976(11) . ?
P2 F8 1.5991(11) . ?
P2 F9 1.6001(11) . ?
P2 F7 1.6041(11) . ?
O1 C4 1.392(2) . ?
O1 C5 1.423(2) . ?
O2 C9 1.375(2) . ?
O2 C10 1.432(2) . ?
N1 C2 1.497(2) . ?
N1 C4 1.497(2) . ?
N1 C1 1.498(2) . ?
N1 C3 1.499(2) . ?
N2 C8 1.491(2) . ?
N2 C7 1.494(2) . ?
N2 C6 1.494(2) . ?
N2 C9 1.524(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F5 P1 F2 90.40(7) . . ?
F5 P1 F6 90.05(6) . . ?
F2 P1 F6 89.97(6) . . ?
F5 P1 F1 89.77(6) . . ?
F2 P1 F1 89.64(6) . . ?
F6 P1 F1 179.56(7) . . ?
F5 P1 F3 179.51(7) . . ?
F2 P1 F3 90.06(7) . . ?
F6 P1 F3 89.80(6) . . ?
F1 P1 F3 90.39(6) . . ?
F5 P1 F4 90.03(7) . . ?
F2 P1 F4 179.55(7) . . ?
F6 P1 F4 90.15(6) . . ?
F1 P1 F4 90.24(6) . . ?
F3 P1 F4 89.51(7) . . ?
F12 P2 F11 90.82(7) . . ?
F12 P2 F10 90.22(6) . . ?
F11 P2 F10 90.54(6) . . ?
F12 P2 F8 90.57(6) . . ?
F11 P2 F8 89.93(7) . . ?
F10 P2 F8 179.08(6) . . ?
F12 P2 F9 90.32(6) . . ?
F11 P2 F9 178.82(7) . . ?
F10 P2 F9 89.80(6) . . ?
F8 P2 F9 89.72(6) . . ?
F12 P2 F7 179.66(7) . . ?
F11 P2 F7 89.52(6) . . ?
F10 P2 F7 89.72(6) . . ?
F8 P2 F7 89.49(6) . . ?
F9 P2 F7 89.34(6) . . ?
C4 O1 C5 110.93(12) . . ?
C9 O2 C10 115.72(16) . . ?
C2 N1 C4 110.79(13) . . ?
C2 N1 C1 109.53(13) . . ?
C4 N1 C1 106.22(12) . . ?
C2 N1 C3 109.69(13) . . ?
C4 N1 C3 110.64(13) . . ?
C1 N1 C3 109.91(13) . . ?
C8 N2 C7 109.77(14) . . ?
C8 N2 C6 109.61(14) . . ?
C7 N2 C6 109.33(14) . . ?
C8 N2 C9 111.06(14) . . ?
C7 N2 C9 107.76(13) . . ?
C6 N2 C9 109.26(13) . . ?
O1 C4 N1 106.89(12) . . ?
O2 C9 N2 111.15(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C4 N1 179.17(13) . . . . ?
C2 N1 C4 O1 -61.56(17) . . . . ?
C1 N1 C4 O1 179.57(14) . . . . ?
C3 N1 C4 O1 60.31(17) . . . . ?
C10 O2 C9 N2 107.01(18) . . . . ?
C8 N2 C9 O2 -62.58(18) . . . . ?
C7 N2 C9 O2 177.16(14) . . . . ?
C6 N2 C9 O2 58.46(18) . . . . ?

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.060

